Contact Information

Author
  • Lionel Delaude
  • Senior Lecturer
  • Chemistry
  • Departement de Chimie
  • Institut de Chimie, Universite de Liege
  • Sart-Tilman, 4000 Liege, Belgium
Email
Phone
+32 (4) 366-3496
Website

Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels-Alder Reaction

Author Contact: l.delaude@ulg.ac.be

Summary

This lab demonstrates a pericyclic reaction that is popular in undergraduate texts, the Diels-Alder reaction, and does so in the context of using water as a safe, alternative solvent. Adapted from work published by Larsen and Grieco in 1985, this experiment makes use of the synthesis of N-benzyl-2-azanorbornene to present green chemistry to students. Not only is this very atom economical reaction performed in water, but the starting materials are fairly low in toxicity, the yields are good and the product does not persist in the environment.

Easily accomplished in a four-hour lab period, this straightforward experiment introduces students to aqueous chemistry, liquid-liquid extractions, drying agents, rotary evaporation, and IR and proton and carbon-13 NMR spectroscopies.

Supplemental information includes an introduction to the Diels-Alder reaction and green chemistry, lab questions, an experimental procedure, spectroscopic data and structural analysis. Also, a poster and slide shows are available in a variety of formats.

Summary prepared January 2009 by Douglas M. Young at the University of Oregon.

Source

Sauvage, X.; Delaude, L. J. Chem. Educ., Print 2008, 85, pp 1538-1540.

J. Chem. Educ. (Abstract only)

Category Descriptors

Chemistry Concepts
  • Alkenes
  • Amines-Ammonium Compounds
  • Aqueous Solution Chemistry
  • Heterocycles
  • Molecular Modeling
  • Pericyclic Reactions
  • Stereochemistry
Laboratory Techniques
  • Extraction
  • Extraction and Drying Agents
  • Heating and Cooling Methods
  • IR Spectroscopy
  • Measuring Mass and Volume
  • NMR Spectroscopy
  • pH
  • Rotary Evaporation
Green Chemistry Principles
  • Design for Degradation
  • Maximize Atom Economy
  • Minimize the Potential for Accidents
  • Prevent Waste
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles